Photoinduced Remote Functionalisations by Iminyl Radical Promoted C−C and C−H Bond Cleavage Cascades | Zendy

Dauncey Elizabeth M. | Zendy; Morcillo Sara P. | Zendy; Douglas James J. | Zendy; Sheikh Nadeem S. | Zendy; Leonori Daniele | Zendy

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Photoinduced Remote Functionalisations by Iminyl Radical Promoted C−C and C−H Bond Cleavage Cascades

Author(s) -

Dauncey Elizabeth M.,

Morcillo Sara P.,

Douglas James J.,

Sheikh Nadeem S.,

Leonori Daniele

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201710790

Subject(s) - bond cleavage , chemistry , cleavage (geology) , stereochemistry , photochemistry , catalysis , materials science , organic chemistry , fracture (geology) , composite material

A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by C(sp 3 )−(sp 3 ) and C(sp 3 )−H bond cleavage gives access to distal carbon radicals that undergo S H 2 functionalisations. These mild, visible‐light‐mediated procedures can be used for remote fluorination, chlorination, and azidation, and were applied to the modification of bioactive and structurally complex molecules.

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